Photosensitized formation of thymine dimers in DNA by tyramine, tyrosine and tyrosine containing peptides

Kaneko, Motohisa; Matsuyama, Akio; Nagata, Chisato

doi:10.1093/nar/6.3.1177

Cited by 8 publications

(5 citation statements)

References 11 publications

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“…Orientation restrictions imposed by the sugar-phosphodiester backbone prevent formation of the anti forms and favour the cissyn arrangement; 19,35,48,[55][56][57][58][59] nonetheless, trans-syn dimers are also observed in ss-DNA or oligonucleotides owing to their flexible structure. 56,60 This is the case of dCpT, TpdC and TpT, which produce mainly cis-syn and trans-syn diastereomers 48,61 in proportions that may range from 7 : 1 (TpT) to 3 : 1 (dCpT) or 1 : 1 (TpdC).…”

Section: Oligonucleotides Photosensitisationmentioning

confidence: 99%

“…For comparison, in direct DNA photolysis the relative formation yields are 1 : 0.8 : 0.2 (TT : CT : CC). 36 Formation of CPDs in isolated and cellular DNA can be photosensitised not only by ketones, 58,76 but also by PyPs, 19,78 NSAIDs, 40,54,68,79 FQs, 23,25,29,[71][72][73][74]80,81 amino acids and derivatives 59,82 or cosmetic agents 83,84 (Fig. 5).…”

Section: Dna Photosensitisationmentioning

confidence: 99%

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Photosensitised pyrimidine dimerisation in DNA

et al. 2011

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aTriplet-mediated pyrimidine (Pyr) dimerisation is a key process in photochemical damage to DNA. 5It may occur in the presence of a photosensitiser, provided that a number of requirements are fulfilled, such as favourable intersystem crossing quantum yield and high triplet energy. The attention has been mainly focused on cyclobutane pyrimidine dimers, as they are by far the most relevant Pyr photoproducts obtained by sensitisation. The present perspective deals with the involved chemistry, not only in DNA but also in its simple building blocks. It also includes the 10 photophysical characterisation of the Pyr triplet excited states, as well as a brief discussion of the theoretical aspects.

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Section: Oligonucleotides Photosensitisationmentioning

confidence: 99%

Section: Dna Photosensitisationmentioning

confidence: 99%

Photosensitised pyrimidine dimerisation in DNA

et al. 2011

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“…Although Tyr is known to be able to photosensitize the formation of thymine cyclobutane dimers in DNA (Kaneko et al, 1979), relatively little is known about its photoreactive properties with any of the nucleobases of DNA. There is suggestive evidence in the literature, however, that such photoreactions could occur.…”

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confidence: 99%

Photoreactions of thymine and thymidine with N-acetyltyrosine

Shaw

Falick²,

Shetlar³

1992

Biochemistry

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We report here the photoinduced formation of a thymine-N-acetyltyrosine adduct. Irradiation of dilute solutions of thymine in the presence of N-acetyltyrosine (NAT) leads to the formation of N-acetyl-4-hydroxy-3-(6-hydrothymin-5-yl)phenylalanine (I), isolated as a mixture of the 5R and 5S diastereoisomers; the photoreaction occurs when irradiation is done either at lambda = 254 nm or at wavelengths of lambda > 290 nm. Irradiation of thymidine in the presence of NAT and of thymine in the presence of tyrosine leads to analogous photoadducts. The photoreaction of thymine with NAT is completely quenched by oxygen and cannot be sensitized by acetone. The likely mechanism involves initial photoionization of the amino acid and deprotonation to form the phenoxyl radical. Thymine then probably captures the released aqueous electron, leading to protonation at C6 of the resulting radical anion. Combination of the phenoxyl and 5,6-dihydrothymin-5-yl radicals would then lead to formation of the final products. The quantum yield for production of the thymine-NAT adduct at pH 7.8 was estimated to be about 5.5 x 10(-4), while a value of 2.3 x 10(-3) was estimated for production of corresponding thymidine adduct at pH 8.1. The dependence of the quantum yield for adduct formation on pH has been determined for both the thymine and thymidine reactions with NAT; the maxima in the quantum yield profiles occur at pH 8-8.5, while appreciable values were measured at pH 7.5. We have also demonstrated that a similar reaction occurs when tyrosine is located within a peptide.(ABSTRACT TRUNCATED AT 250 WORDS)

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“…0006-2960/83/0422-1390$01.50/0 © 1983 American Chemical Society basis. This mechanism continues to be important in the UV-B region, but in addition, photosensitization (Kaneko et al, 1979; Sutherland & Griffin, 1980) and indirect action contribute to damage formation (Elkind & Han, 1978; Netrawali & Cerutti, 1979). Cyclobutane-type dimerization represents the predominant photoreaction of DNA even in the UV-B region.…”

mentioning

confidence: 99%

Cyclobutane-type pyrimidine photodimer formation and excision in human skin fibroblasts after irradiation with 313-nm ultraviolet light

Niggli¹,

Cerutti²

1983

Biochemistry

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The formation and excision of 313-nm light-induced cyclobutane-type pyrimidine photodimers were determined in confluent cultures of human fibroblasts. A new method was developed for the resolution and determination of cytosine-thymine (CT) and thymine-thymine dimers (TT) by using sodium borohydride reduction and high-pressure liquid chromatography. This assay can detect as little as 1.8 TT or 5.6 CT per 10(8) daltons, levels induced in monolayers of human skin fibroblasts by doses of 1 and 2 kJ m-2 of 313-nm light, respectively. CT formation was 20% more efficient than TT formation in the physiological dose range of 2.25-15 k m-2 at 37 degrees C. Normal fibroblasts removed 61% TT within the first 8 h of incubation following a dose of 5.5 kJ m-2. CT was removed approximately twice as efficiently as TT during the same time period following exposure to 10 kJ m-2. The lack of removal of CT as well as TT observed in xeroderma pigmentosum fibroblasts indicates that the repair deficiency in these cells affects the repair of both classes of dimers.

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Photosensitized formation of thymine dimers in DNA by tyramine, tyrosine and tyrosine containing peptides

Cited by 8 publications

References 11 publications

Photosensitised pyrimidine dimerisation in DNA

Photosensitised pyrimidine dimerisation in DNA

Photoreactions of thymine and thymidine with N-acetyltyrosine

Cyclobutane-type pyrimidine photodimer formation and excision in human skin fibroblasts after irradiation with 313-nm ultraviolet light

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